Diethyl Ether → 1-benzyl-5-fluoro-3H-indol-2-one

HRID 447494Notes

Reaction equation

HRID 447494 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6](=[O:18])[C:5]2=O.CCOCC>CCCCCC>[CH2:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[CH2:5][C:6]1=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 110971561-Benzyl-5-fluoroindoline-2,3-dione

Product 1

HCID 149184901-benzyl-5-fluoro-3H-indol-2-oneYield 75.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a manner similar to the method of N-benzylisatin, 5-fluoroisatin (10.0 g, 60.5 mmol) yielded 5-fluoro-N-benzylisatin as an orange red powder (14.5 g, 93%). The crude product was used for the next step without purification. 1H NMR (400 MHz, CDCl3) δ7.33-7.21 (m, 5H), 6.95 (d, J=7.6 Hz, 1H), 6.84 (t, 1H), 6.60 (m, 1H), 4.89 (s, 2H); MS ESI 255.9 [M+H]+, calcd for [C15H10FNO2+H]+ 255.07. The title compound was prepared in a manner similar to the method of N-Benzyl-oxindole using 5-fluoro-N-benzylisatin (14.5 g, 56.8 mmol). Trituration using Et2O:hexane yielded the title compound as a pale yellow solid (10.3 g, 75%). 1H NMR (400 MHz, CDCl3) δ 7.30-7.26 (m, 5H), 7.00 (d, J=7.6 Hz, 1H), 6.87 (t, 1H), 6.63 (m, 1H), 4.91 (s, 2H), 3.63 (s, 2H); MS ESI 241.9 [M+H]+, calcd for [C15H10FNO2+H]+ 241.09.

Workup

  1. customThe crude product was used for the next step without purification
  2. customThe title compound was prepared in a manner similar to the method of N-Benzyl-oxindole

Sources & evidence

ORD record
ord-c598501d8daf478c88da0e517c2c3484
Source dataset
uspto-grants-2013_07
Patent number
US08481525B2

Reaction notes

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